


Starting At the End

by Cobrilee



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Derek Hale/Top Stiles Stilinski, Brief mention of Derek's past canonical relationships, Canon up to 5B, Confident Stiles, Experienced Stiles Stilinski, Explicit Sexual Content, M/M, Masturbation, Mention of post-high school Stiles/Danny, Phone Sex, Praise Kink, Rimming, Stiles Takes Care Of Derek, Stiles and Derek shower together, Stiles educates Derek sexually, Stiles is an amateur porn star in college, Top!Stiles, bottom!Derek, brief angst, inexperienced Derek Hale
Language: English
Status: Completed
Published: 2016-10-19
Updated: 2016-10-19
Packaged: 2018-08-23 08:53:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 17,775
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8321692
Author URL: https://archiveofourown.org/users/Cobrilee/pseuds/Cobrilee
Summary: After graduating college and quitting his amateur porn gig to move back to Beacon Hills and join the Beacon Hills Sheriff's Office, Stiles discovers that the man he never quite left behind is now a... fan. Leave it to the two of them to start at the end.





	

**Author's Note:**

  * For [clotpolesonly](https://archiveofourown.org/users/clotpolesonly/gifts).



> WARNING! This fic depicts Stiles having sex with OMCs, as he becomes an amateur porn star in college. The Stiles/OMC sex is brief, but it exists, and it's to show the difference between Stiles when he's working, and Stiles when he's emotionally invested. It is not written to be sexy or erotic, it's all business. 
> 
> I say this because I know there will be people who can't get past the idea of it to read the fic, and I don't want to upset anyone who didn't know what they were signing up for. That said, I WILL DELETE ANY COMMENTS COMPLAINING ABOUT IT. This is why warnings exist.
> 
> ALL THE LOVE AND HUGS AND SQUISHES TO THE BEAUTIFUL AND AMAZING Rachael/maiNuoire for holding my hand through this whole thing, beta-ing at the last minute, and putting up with me sending screenshots of snippets because I was too impatient to actually finish the scene before sharing. Seriously, y'all, Rachael is the mutherfuckin best.
> 
> Request in the end notes.

Moans and grunts fill the airy, spacious room, and yet Stiles’ brain is racing ahead to the finish line instead of focused on what he’s doing. His mind isn’t on the guy behind him, lifting his leg slightly in the air as he pounds into Stiles’ ass; he’s thinking about finishing up, getting showered. Heading home to grab his suitcase, duffel, and the last couple boxes of miscellaneous stuff, stowing them in the back seat of the Jeep, and heading back to Beacon Hills.

“Fuck, babe, you feel so fucking good around my dick!” his partner, Vic, groans. “Your ass is so tight and hot!”

Stiles mentally rolls his eyes. He’d long ago become accustomed to the horrible “acting” part of his job, the cheesy dialogue that was pretty much a staple of the porn industry, but it doesn’t mean he doesn’t still groan in something other than pleasure whenever he has to listen to it-and worse, speak it. Luckily, Trevor doesn’t ask them to talk their way through fucking. Some grunts and groans and “fuck yeah”s were good enough in his book. And apparently their subscribers’.

“Oh God,” Stiles pants out, reminding himself to get back into character, thrusting back against Vic and grinding into his crotch. He wills his cock to stay hard enough for him to stroke himself to completion in a few minutes. They’ve been going for about fifteen, so the money shot is imminent. “Fuck my ass, baby, pound me, come on, make me come!” He forces himself not to wince at the ridiculousness of the words, instead focusing on the way Vic starts picking up speed, thrusting harder.

He can see Joey tapping his watch behind the camera, and Stiles reaches down, gripping his cock with tight fingers. He times his strokes with Vic’s, squeezing on the upstroke as Vic slams into him, and he can feel the tingle starting to spread through him. He starts panting and groaning for real, the sensations crawling up his spine and splintering through his nerve endings, and he moans out a loud “fuck!” when he starts spurting. He’d purposely refrained from jerking off that morning as well as the previous day, knowing it was going to be his last shoot, which results in an impressive amount of come striping over the cobalt-colored sheets. Since he’s lying on his side as Vic fucks into him from behind, the first energetic bursts coat the inside of his forearm, with droplets landing on his stomach and inner elbow as well.

Vic yells his way through his orgasm, pulling out and stripping the condom off before pumping his come onto Stiles’ ass. Stiles has always privately found it annoying and a classic example of overacting, but whatever. Vic’s dick was the biggest, and Trevor wanted him to be the one to fuck Stiles for his last video. As much as their subscribers liked watching Stiles top, the biggest hits always came when he was bottoming, so Trevor thought his farewell video should have him getting spread out on the biggest cock in their stable.

Stiles dutifully cranes his head back a little, allowing Vic to grab his chin and plant a “loving” kiss on his lips, but when Joey waves to get their attention, Stiles breaks away, knowing the camera has faded to black. 

Vic rolls over and off the bed, dropping the used condom in the trash and grabbing one of the towels Eva is holding out. Stiles isn’t sure why; after all,  _ he’s _ the one who ended up covered in come. Not that he’s complaining. He’s used to it by this point. 

He takes the other towel from Eva, dropping a quick kiss on her cheek. “I’m going to miss you, Eves,” he sighs. “You always take such good care of us.”

“Like you’re not going to be able to get your own towels and water bottles from now on,” Eva scoffs, but Stiles knows she’s a little sad to see him go. They’re almost like a family at this point. The whole set-up is Trevor’s, but Eva’s been with him since he started collecting studs for the stable, so she’s almost like a big sister. If big sisters watched you fucking other men for money on a regular basis. Which, ew. Disturbing. It makes Stiles glad he doesn’t actually have a sister, because  _ that’s _ a mental image he would never be able to get rid of.

Vic high-fives him after wiping the sweat from his face and body and dropping the towel on the bed. “I’m gonna miss fucking that sweet ass of yours,” he concedes, eyeing said ass appreciatively, and Stiles snorts.

“You’re such a charmer,” he retorts dryly, and Vic shrugs. Stiles has never really felt skeevy about what they do, but if he did, it would be because Vic himself is a little on the skeevy side.

Joey and Trevor hang back a little while Stiles finishes wiping off and pulls his underwear, jeans, and tee back on. The towel didn’t get all the residue off so the clothes stick a little bit, but it’s good enough until Stiles can get back to his apartment and take one last shower. Once he’s dressed, though, the two men step in and take turns hugging him goodbye. 

“If you ever want to come back and start working again, let me know,” Trevor reminds him, clapping him on the back. “You know our subscribers are going to be broken-hearted when their favorite switch-hitter disappears from our line-up.”

Stiles laughs. "Thanks for the offer, but I have a life waiting for me back in Beacon Hills. This was fun, but you know it was always meant to be temporary."

Joey smirks. “I can’t believe you’re trading having sex all day to be a deputy with your old man. You could be eating assholes instead of arresting them.” 

“As beautiful as that imagery is, Joe, this is what I’ve wanted since my senior year,” Stiles reminds him with a chuckle. “I haven’t spent the last four years getting my Criminal Justice degree so I can spend the next fifteen on all fours while I take a dick in my ass.”

“You’ll do that anyway,” Gavin teases him, entering the room just in time to say their goodbyes. He gives Stiles a tight hug. “You know you can always come back for a hookup, even if you’re not working, right?”

“I’m pretty sure I won’t have to drive six hours to get laid,” Stiles retorts. Tilting his head, he reconsiders his words. “Although we  _ are _ talking about Beacon Hills. My options will probably be limited.” He glances around. “Where are Kirk and Ryan? Are they really going to let me go without saying goodbye?”

Trevor shakes his head. “They’re in the sunroom. We’re doing their shoot next, so they’re getting prepped.”

Stiles smirks, knowing that basically means they’re shoving lube up their asses and jerking themselves a little bit so it doesn’t take too long to get hard once the camera’s going. “I’ll swing by on my way out."

Eva presses another kiss to his cheek. “Don’t be a stranger, Stiles. You don’t have to forget us just because you’re not working with us anymore.”

“Forget my favorite girl? Never!” he cries in mock offense, and she rolls her eyes and shoves him away playfully. He high-fives the rest of the guys, minus Vic, before shrugging his backpack on over one shoulder and stepping out of the bedroom for the last time.

It feels odd, descending the staircase and knowing he’ll never be back. He’s filmed a lot of videos with these people over the past three years, has spent a lot of his non-educational time in one of these rooms in any number of positions. He knows, despite his claims to the contrary, that he’s going to miss it. 

“Stiles!” Kirk yells as Stiles pokes his head into the sunroom. Both of them are sprawled on the couch, fists lazily stroking up and down their cocks and keeping them half-hard while Joey brings the camera setup downstairs. “You out of here, bro?”

“Yup. Promised my dad I’d be back in Beacon Hills by the time he goes to bed. Which doesn’t give me a lot of time, considering he’s old and goes to bed after the news,” Stiles jokes. “Just wanted to say goodbye before taking off.”

It doesn’t even feel weird when they both stand up and grab him around the neck, their dicks digging into his hip on either side. He’s lost count of the number of times he’s had one of those dicks inside him, or his inside one of them. 

“I’m gonna miss you, man,” Ryan pouts, the same routine he’s pulled every summer of their college experience, and Stiles grins at him with genuine affection. He’s going to miss Ryan too, his best friend for the last four years, the person who introduced him to the world of jacking off on webcams for money and started the whole chain of events that landed him in Trevor’s amateur porn production. “Come back and see us some time, yeah?”

“You know it,” Stiles promises him, turning his head at the last second to brush a quick kiss across his cheek. “Stay in touch.” He feels almost like a walking high school yearbook, but the smiles Kirk and Ryan toss at him as he waves and heads for the front door ease the sensation of cheesiness.

It isn’t until he’s tugging open the Jeep’s front door that it really hits him. His amateur porn career is over. No more fucking on film and watching the hits climb, along with his bank account balance. Now he has a mature, responsible life to look forward to; a life as a Beacon Hills Sheriff’s Department deputy, where he’ll be an upstanding officer of the law.

It makes him wonder how many times he’ll be protecting and serving someone who’s seen his bare ass getting plowed. He snickers, climbs in the Jeep, and slams the door behind him.

\-----

_ If someone had told him when he started freshman year that Stiles would be sitting on his bed his first week back from winter vacation, staring down at his dick and legitimately contemplating whipping it out and jacking off on camera, he would have been… well. He would have been intrigued. Laughed it off a little nervously. But he would have thought about it at night when he was jacking off just for himself instead of a viewing audience. _

_ Which is pretty much the entire reason it didn’t take much effort for Ryan to convince him to try it. _

_ Ryan, who was both the angel and the devil on his shoulder and who had become Scott v2.0 since Scott up and fucking went to Buenos Aires, of all places, after graduation. It was Chris’ new “I’m going to forget that my entire family is either dead or psychotic, and in some cases both” destination vacation, and he’d invited Scott to join him and Isaac for some time, forget about the horrors of high school in Beacon Hills. Stiles really couldn’t blame him, but shit, he hadn’t expected Scott to defer his freshman year and abandon Stiles. _

_ But it’s cool. He has Ryan, who is fucking awesome, and he’s not as lonely as he was those first couple weeks. _

_ If Ryan is like a poor man’s version of Derek Hale, well, that has nothing to do with why Stiles likes hanging around him. Honestly, it’s a testament to Ryan’s awesomeness that Stiles is willing to hang out with him despite the constant bombardment of memories, and lust, and lusty memories, that his presence generates. _

_ So yeah, when Ryan suggested he jerk off for money, in response to Stiles’ laments that a full-ride scholarship was great when it came to school expenses, but not so much when it came to pizza and beer (shut up, all freshmen drink, it’s like a rule of college or something), Stiles didn’t immediately scoff and reject the idea outright. He snorted, rolled his eyes, and made a traditionally self-deprecating gesture at his body, as if to illustrate the point that no one would pay money to watch him yank on his dick. _

_ “You know you’re fucking gorgeous, right?” Ryan had asked him, staring at him without irony, and Stiles flailed a little. “Your body definitely fits a type. Not everyone wants some muscle-bound beefcake, you know. Your eyes are beautiful, your smile makes people want to know you, and those hands are meant for fantasizing about. You start stroking yourself on-camera, and any guy watching you will spend the next month imagining you doing the same thing to them. And they’ll come back, spending money to keep buying into that fantasy.” _

_ Stiles had gaped at him, stunned. Ryan was dead serious, and it was clear it wasn’t even a little bit about bolstering Stiles’ deflated sense of self. He really believed Stiles could make money doing what he loved doing more than anything else.  _

_ “Wait, how do you know so much about this?” _

_ Ryan smirked at him. “I’ve been doing it since I turned eighteen. Older guys love watching younger men. And they’ve got the money to keep me interested in showing off.” _

_ Which… didn’t bother him as much as it once would have. Stiles’ sexuality crisis hadn’t exactly been a crisis. Once he realized there was a  _ reason _ he was constantly pestering Danny about whether he was attractive to gay guys (the reason being he wanted to know if he was attractive to  _ Danny _ , because he was attracted  _ to _ Danny), and then Derek pretty much became his go-to for spank-bank material in junior year, it was less a crisis than a, “Huh. Dudes do it for me” revelation. He was okay with that. _

_ So when Ryan suggested Stiles watch his cam one night, to kind of get an idea what to do and how it worked, Stiles didn’t really hesitate.  _

_ And now… Now he was fiddling nervously with the drawstring on his sweats, glance flickering over to the webcam embedded in his laptop, and taking a deep, shuddery breath. He was really going to do this. Ryan had helped set him up with an account, had shown him how to log in and schedule and arrange everything, and it was a few minutes before his first show.  _

_ His sheets were clean and his bed was made, all of his stuff pushed out of the shot; the only thing visible was his lamp and a bottle of lube. Ryan had cautioned him against going straight for the toys, said it was better to start simple and introduce new stuff as he built up a following. The concept was slightly ludicrous to Stiles, that he could have a following of people who just wanted to watch him play with himself until he came. _

_ Then again, after watching Ryan, he could see the appeal. It was different than regular porn, it was interactive. Ryan paused periodically and read his chat and responded to people’s questions or comments, and he made it seem like he was putting on a show just for the viewer. Stiles had forgotten for a few minutes that Ryan was his buddy. He became the guy Stiles was dying to hit his knees for, to suck down that gorgeous cock. _

_ And in just a few minutes, he would, hopefully, be that guy for someone else. _

_ Anxiously, he turned on his webcam, logged into the site. Ryan had cautioned him to not expect good numbers, not at first. He needed to get ratings and comments and bump up the featured list, which would take some time. _

_ It still didn’t make it easier to wait for nearly five minutes before the first person joined the session. But once they did, Stiles smirked at the camera and hooked his thumbs in his sweats, tugging them down slowly as he sank onto the end of the bed. His cock was still soft in his underwear, but he figured that was to be expected. He remembered that Ryan had started slowly, massaging himself through his underwear, and he decided to try to emulate Ryan’s style. At least at first, until he figured out what worked best for him. Having that settled, he palmed himself through the black cotton of his briefs, rubbing himself slowly, working his hand over his length as it gradually began to fill. _

_ After about a minute the person left the session, and Stiles’ spine stiffened. He wanted to call Ryan, to demand to know what he did wrong. For the moment, he froze as he wavered on whether he was supposed to keep going or wait to see if someone else joined. It didn’t make much sense to jerk off with no one there to see him. _

_ Well, it  _ always _ made sense to jerk off. But if he was doing this to get paid, it only made sense to do it when there were people there to pay. _

_ Before he could talk himself into logging out and turning off his cam, someone else joined the session and he breathed an imperceptible sigh of relief. Easing back, letting his shoulders drop forward and his abs curl in, he gripped the beginnings of his erection through his briefs, stroking upward languidly. Another person joined the session, and his spirits began to perk up along with his cock. _

_ After that first session, it got easier. By the time his release was spurting over his stomach, come dripping into his navel, there were eight people watching and making comments about how they wanted to add their mess to his, or they wanted him to come on their faces. It was weird to read, and Stiles wasn’t sure if it made him uncomfortable or just fascinated. The next time he logged in, he ended up with nineteen watchers, and the third time he had twenty-seven. His confidence skyrocketed, and he learned how to smirk a little more, shift his hips teasingly, add a little swagger now and then. It became second-nature to him to to turn on the cam, strip down, and stroke himself off while adding enticing sound effects and pausing now and then to address comments that popped up in the chat box. _

_ It really shouldn’t have surprised him when he got the request to start doing partner videos. _

\-----

“Yo, Scotty!”

Scott looks up as Stiles enters the diner, a huge smile splitting his face. “Stiles!” he calls out, and the diner’s few patrons glance up from their conversations to flick their frowns back and forth between the two; neither of them pay any attention. “Buddy, you made it!” Scott exclaims as he leaps up from the booth, wrapping his arms around Stiles and pounding enthusiastically on his back.

“Scott, I’m still a fragile human. You’re going to crack some ribs,” Stiles wheezes, and Scott pulls back sheepishly. “It’s good to see you again.”

“It’s been too fucking long, man,” Scott agrees, sliding back into the booth as Stiles sinks into the bench on the other side. 

He glances around. “Where’s everyone else? I thought this was going to be a reunion type thing?”

“They’ll be here in a little bit,” Scott informs him, pulling out the menu but continuing to beam at Stiles. “I told them we needed some bro time first.”

“Meaning you want to wax poetic about your new lady love,” Stiles guesses with a snort. Scott’s smile goes from beaming to blinding, and Stiles pretends to shade his eyes against the glare. 

“Oh man. Stiles. She’s it, really, she’s the one.” He sighs dreamily, and Stiles bites his tongue to refrain from mentioning that he’d thought Allison was the one. It wouldn’t be fair to bring up his dead first love while he’s going on about the newest. “Naomi is amazing. She’s so smart, and funny, and  _ gorgeous _ -”

Stiles can’t take it anymore. He loves his friend, but really, a few years away from him had lowered his tolerance for rhapsodic testaments of love. “Have you bought the ring yet?” he interjects, and Scott blushes a little, and Stiles groans, because yep. He’s totally bought the ring already. “How long has it been this time?”

A hurt frown appears on his face and Stiles sighs, mentally kicking himself. “It’s been six months,” Scott answers quietly, and Stiles tries to smile. Tries to, being the operative phrase. “I know it’s fast, but neither of us has ever felt like this before.”

It’s on the tip of his tongue to remind Scott that he says the same thing every time, but he’s already hurt his friend’s feelings once. Besides, Scott is twenty-two now. Maybe it really is different. “I hope she says yes,” is what he says instead, and the sunny grin appears on Scott’s face once more.

Before Scott can continue enumerating all of Naomi’s wonderful qualities, Liam flings the diner door wide open and smirks when he sees Stiles. “Hey, asswipe,” he greets him cheerily, and yet again, the few diners look up and frown disapprovingly. Mason bops in behind him, smiling brightly when he catches Stiles’ eye and waves. Stiles waves back; he actually  _ likes _ Mason. Liam isn’t so bad anymore, he supposes, but they still maintain their semi-friendly antagonistic sneering. 

They fall in beside he and Scott; Liam plopping down next to his alpha and Mason sliding in beside him. “It’s great to see you, man,” Mason enthuses. “College was good to you.”

Stiles shrugs; he lost any sense of modesty a long time ago. “Finding a place you belong tends to help you get comfortable in your own skin,” he acknowledges, and Liam snorts, so Stiles frowns at him. He’s expecting some kind of joke about his career choices, as it’s a secret from exactly no one in their pack. From any of their parents, either, to Stiles’ eternal regret. He hadn’t exactly intended for his dad to find out, but his dad knew he was bi and how much he loved sex, so awkward conversation aside, it hadn’t been terribly painful. It wasn’t until the day Scott had mistakenly spilled the beans in front of Melissa that Stiles, for the first time ever, lamented his poor choices. 

The expected insult doesn’t come, however, and Stiles can appreciate that Liam has learned how to keep his mouth shut. “So are you back for good?” he asks instead, and Stiles nods in confirmation.

“I start with the Sheriff’s Department in a month, when Walton retires,” he explains, referring to Deputy Royer. He was the only old-timer the department still had, besides his father; he’d been on medical leave during the massacre when Stiles was in high school, which was how he survived all the younger deputies. He was finally ready to take his fishing pole and waders and bid them all adieu. Stiles would be filling the space his retirement generated. It was damn good timing; Stiles liked to think Walton was just waiting for him to graduate before leaving a position open.

“Whatever, I’m just glad you’re back,” Scott grins, and Liam rolls his eyes.

“Me, too,” he says emphatically. “Now he has someone else to blab to about Naomi.”

Scott glares, but he’s not using the red eyes, so Liam ignores him. As much as Stiles is dying to wade into that minefield (he’s really not), he focuses his attention elsewhere. “Is this everyone?” he asks, glancing around. He knows Lydia is still in Boston, and Kira hasn’t been back since she left during the middle of senior year. He vaguely recalls that Malia decided a couple years ago to resume being a coyote, like, 95% of her time, with occasional bouts of humanity to visit her dad, but surely there should be others left, right? 

“Let me guess, you’re asking about Derek or Danny,” Liam scoffs. “Which one is it? The guy you fucked for an entire summer, or the guy you  _ wished _ you got to fuck for an entire summer?”

Stiles scowls at Scott. “What kind of manners are you raising this boy with?” he grumbles. “His language is atrocious. Also, what the  _ fuck _ , Scott? You  _ told  _ him?”

Before Scott can answer, Liam interjects with a roll of his eyes. “No one had to tell me anything, dipshit. I could smell you all over Danny, and Danny all over you, for a whole summer. And Jesus, you and Hale’s sappy-puppy eyes pining at each other was nearly enough to make me vomit. Until he left, anyway. Also, seriously? You did gay porn for money for three and a half years. You’re no one’s moral high ground, Stilinski.”

Stiles knows Liam isn’t  _ really _ slut-shaming him, but the mocking tone of his voice still makes him bristle. Liam had long ago grown out of his temper, but unfortunately he’d grown into his sassiness at around the same time. “You just  _ wish _ you had my bank account, Dunbar.”

“Boys,” Scott warns, and Stiles makes a face at Liam, who makes a face right back. “Danny hasn’t been around since that summer, and Stiles knows it, Liam. Stop antagonizing him.” He flicks an apologetic glance at Stiles. “And Derek, um. Derek said he didn’t plan to join us.”

“He hates you,” Liam informs him, voice taunting, and Scott sighs in exasperation.

“That’s not true,” he tells Stiles, frowning at Liam. “I think there’s something else going on, though. He… Well, he smells odd when your name is brought up.”

Stiles knows Derek’s only been back for a month, so he wonders how Scott has managed to talk to him about Stiles enough to notice a pattern. “Odd?”

“Embarrassed,” Liam clarifies.

Stiles glares at him, annoyed. “What, do you trail after Papa Scott to listen in on every werewolf-related conversation he has?” he snarks, and beside him, Mason is trying not to snicker. He takes that as a yes. “How do you know so much about Derek and what he smells like?”

“Because he pesters Scott all the time about when you’re coming home,” Liam answers smugly, folding his arms across his chest. “I can’t help it if he interrupts pack time with his neediness.”

“Liam, stop being an ass,” Mason scolds, and Liam shrugs. Mason turns to Stiles, eyes conveying apologies for his best friend’s behavior. It’s nothing Stiles hasn’t learned to expect, but it’s nice that at least someone feels bad on his behalf. “It’s only been a couple times,” he reassures Stiles, though Stiles has no clue what he needs to be reassured for.

Derek has been asking about him? Derek wants to know when he’ll be home? Why? Is he planning on leaving again before he can see Stiles? But Liam said Derek was embarrassed… Although that tidbit came from Liam, so it should definitely not be taken at face value.

“Who knows?” Liam muses, smirking. “Maybe he watched your videos and now he can’t imagine looking you in the face.”

“Yeah, right,” Stiles scoffs. “Derek Hale couldn’t  _ be _ any straighter. I can guarantee you he’s never seen one of my videos.”

\-----

_ “Have you ever considered doing partner scenes?” _

_ Stiles blinked at Ryan, tilting his head to one side as he rolled the thought around in his brain. “I wouldn’t be opposed to it,” he said finally. “I hadn’t thought about it, but it’d probably be more lucrative than solo videos. And I love sex.” Not that he’d had much since the previous summer, when he and Danny had hooked up at least once or twice a week, but he knew he liked it. A lot. “What brought this on?” _

_ Ryan shrugged, the effort in making it a casual gesture both obvious and concerning. “I was approached by an amateur porn company that operates just off campus. They saw my videos and wanted to know if I’d be interested in partner work, too.” _

_ “What’s the catch?” Stiles asked suspiciously. _

_ “They want an audition video,” Ryan admitted, wincing. “With someone who isn’t one of their people already.” _

_ “You want to fuck me,” Stiles realized flatly. “So you can get a better job.” _

_ “It’s not a trick to, like, get you to sleep with me,” Ryan rushed to assure him. “I just figured you’re already comfortable with cam work, and we’re friends, and I trust you. Besides, I’ve already told you you’re hot. Fucking you wouldn’t be a hardship.” He tried out a cheesy wink, and Stiles couldn’t help it, he laughed. _

_ Leaning back in his desk chair, biology paper forgotten for the moment, Stiles studied him. “You think they’d be interested in a two for one?” he asked mildly. “You know, if they like the video?” _

_ Ryan nodded. “I can almost guarantee it. They don’t have anyone who looks like you, and you’d bring in a new demographic. We don’t get paid if we don’t get hits, so it doesn’t hurt them to bring in another cast member.” _

_ “Cast member,” Stiles scoffed, smirking. “It sounds so legitimate.” He chewed on the end of his pen, thinking. “Alright, so who’s bottoming, and when are we doing this?” _

_ The video was a hit. Trevor’s company put it up as the featured video on their website for the first week, to introduce the two new members of their house, and it generated so many hits in that week that Trevor decided Stiles and Ryan were the new dream team and they would be doing their videos together for the foreseeable future. _

_ It took two months before Stiles topped Ryan for the first time. Ryan had wanted to top in their first video, thinking he would appear more powerful and make a more favorable impression, and it had gone over so well that Trevor continued to script scenarios where Ryan topped. Stiles didn’t mind, he liked bottoming, but finally he approached Trevor and informed him he was actually versatile, and wanted to top sometimes as well. The news had surprised Trevor, but their very next shoot had Stiles and Ryan switching-after confirming that Ryan was okay with it, of course. _

_ As he had done innumerable times the past two months, Stiles envisioned a different dark-haired man as he went into the scene, imagined a different face staring down at him, mouth falling open when Stiles nearly inhaled him. As he sank into the man beneath him, Stiles imagined pale green eyes peering up at him, half-glazed from pleasure, and when he came, it was Derek’s voice he heard crying out with his own release.  _

_ He didn’t feel guilty using fantasies of Derek to get him through the actuality of fucking his best friend on camera. It wasn’t like they were dating, and their sexual activities extended solely to their work, so Stiles continued to think of Derek so his and Ryan’s off-camera friendship didn’t suffer. If anything made him feel even a little bit guilty, it was the thought that Derek would be upset to know he was Stiles’ fantasy material. Derek was straight, and he’d barely tolerated Stiles by the time he left for parts unknown. Stiles felt like maybe it was a violation of the pack-lite relationship they’d begun to establish for him to get off to thoughts of burying his cock in Derek’s tight ass. _

_ Trevor had congratulated him after that scene. Said he hadn’t really seen Stiles as a top but gave him the chance because he wanted him to be happy at work instead of going elsewhere, and watching them had convinced him that Stiles was versatile indeed. They’d come up with a schedule of switching it up, and Trevor had even suggested changing partners for the first time. He wanted to bring in another new guy, Joey, who was a dedicated bottom, and he thought Stiles would be the best one to initiate him. Stiles was happy to agree to the new course of action. _

_ Over the years, Stiles moved easily through their lineup. He bottomed with Vic, topped with Joey, switched with Ryan and Kirk, and did all manner of things he’d never imagined before. Or, well, he could imagine them, but he’d never imagined himself doing them. His sexual repertoire and education flourished, and he came out of it feeling wildly confident and so laid-back about sex that it amazed his friends, the one who’d known him long before his new sexual maturity. There wasn’t anything that could surprise him. _

_ Until the first time he ran into Derek Hale, post-graduation and return to Beacon Hills. _

“Stiles.”

He jerks at the unexpected sound of Derek’s cool, polite voice; then scowls when he realizes it’s cool and polite. “Fuck you.”

An eyebrow arches. “Excuse me?”

“You heard me.” He’s itching to get his face punched, apparently. Oh well. He isn’t in film anymore, he doesn’t need to worry about preserving his good looks-such as they are. “Fuck you.”

“Mind telling me what I did to bring on that kind of ire?” His tone is mild, but Stiles can hear the irritation under it.

He snorts in derision. “I’ve been back in town for almost three whole weeks, and you’ve avoided me like the goddamn plague. When we have pack nights, you never show up.”

“Technically, I’m not part of the pack,” Derek points out, but Stiles ignores him. He won’t be dissuaded by facts and logic.

“Beacon Hills isn’t small, but it isn’t big, either. You’ve been avoiding me,” Stiles accuses.

Derek has the good grace to look abashed, the tips of his ears pinking slightly. “Not entirely,” he hedges, and Stiles rolls his eyes in exasperation. “I’ve been spending a lot of time working from home. I haven’t made an effort to see you,” he acknowledges, “but I also haven’t gone out of my way to  _ not  _ see you.”

Stiles eyes him suspiciously. “That twist of words sounds a lot like something I would say.”

“I learned from the best?” he offers, a charming smile lighting his face, and fuck, Stiles is so screwed.

He blows out a breath, sinking down onto the bench outside his dad’s office. “What are you doing here, anyway?”

Derek holds up an envelope. “Getting a copy of my fingerprint records.”

“Why does the BHSO have a copy of your fingerprints on file?” Derek levels a half-hearted glare at him, and Stiles flushes. “Oh. Yeah. Sorry?”

He makes a sound that’s approaching a chuckle, but Stiles has to have heard wrong. Derek Hale doesn’t chuckle. He doesn’t laugh. He doesn’t snicker. He glowers and growls and smolders, but he doesn’t express mirth. “It was six years ago, Stiles. I’ve forgiven you.”

“Yeah, well, you should have never been upset with me in the first place.”

Both eyebrows climb into his hairline. “You accused me of murder. Of murdering my  _ sister _ . You got me arrested.”

“Maybe, but I was just trying to make sure her killer was apprehended, and really, shouldn’t you have been grateful I cared?” Stiles defends himself, and all of a sudden, the apocalypse is upon them. Or Stiles thinks it must be, because a grin is curving Derek’s lips, and then it grows into a smile, and then it’s almost taking over his face, and yes, yes, there’s a chuckle. A real one, an unmistakeable one. Stiles is sure the world is ending.

“It’s been almost five years since I’ve seen you, and somehow I thought you would’ve changed by now,” Derek sighs, though amusement laces his tone. “It’s nice to know you haven’t changed at all.”

“Shows how little you know,” Stiles mutters. “I’ve changed a lot. I’ve definitely grown up,” he adds challengingly, and what the hell is that? Is that a… holy fuck, Derek Hale is  _ blushing. _ And suddenly, he’s reminded of Liam’s assertion that Derek smells embarrassed when they talk about Stiles. “Is there something you want to tell me?” Confidence blooms in his voice, a cocky smile pushing its way onto his face, and he sprawls back on the bench, loose-limbed and sly.

Derek swallows. “I don’t know what you’re talking about.”

“Bullshit,” Stiles scoffs. “Liam might be a little shit, but he rarely lies to me these days. Mostly because he enjoys tormenting me with the truth, but whatever. He said you smell embarrassed when my name gets brought up in conversation.” And maybe Stiles doesn’t have werewolfy scenting superpowers, but he’s a pretty astute observer of human behavior, and yep, that looks a lot like embarrassment clouding Derek’s gorgeous features.

Before Derek can come up with a response, the door to the sheriff’s office opens and John is stepping out, smiling tiredly when he sees Stiles and Derek. “Son. Derek,” he adds, nodding at Derek, who responds in kind. “You ready to head out?” he asks Stiles, who frowns at the relieved expression that crosses Derek’s face.

“Sure, Pops,” he answers agreeably, and the two of them stand. Stiles studies Derek, who stares back at him wordlessly. “It was nice to see you, Derek. Let’s do this again in another five years?”

Derek makes a face at him and Stiles flashes a winsome grin in return. “I’m sure it won’t be that long,” he returns easily, and if Stiles didn’t know better, he’d think that low purr was almost a  _ promise _ . “Sheriff,” he acknowledges, before turning and exiting the station. 

John casts a bemused glance at the door Derek just departed through. “Is there something I need to know, Son?” he asks, and Stiles sighs. 

“Fuck if I know, Dad. Fuck if I know.”

\-----

It takes Stiles four whole days before he gathers the courage to text Derek. 

_ S: Back to ignoring me, Sourwolf?  _

_ D: Stiles, it's been five years. Can we please put that nickname to rest?  _

_ S: Never. It's a classic.  _

_ D: It was worth a shot.  _

_ S: You're ignoring my question.  _

_ D: I'm not ignoring you.  _

_ D: I thought we had this conversation.  _

_ S: We did, but that reminds me there's another conversation we were having that got interrupted. _

_ D: I thought everything was resolved.  _

_ S: Why are you embarrassed when someone else talks about me?  _

_ D: I'm embarrassed for them, that they still know you.  _

_ S: Wolfy’s got jokes.  _

_ D: I'm not embarrassed, Stiles.  _

_ S: Then why does Liam think you are?  _

_ D: Because I have a very specific memory associated with you that comes to mind every time you do.  _

_ S: And that memory is…?  _

_ D: Jensen DeSteele _

Stiles drops his phone like it's burning a hole in his hand. Jensen DeSteele had originated as a joke, when the guys were talking about porn names. Stiles had offered his suggestion up with a laugh, then sputtered in indignation when nobody got the reference. He'd turned a couple of them into Supernatural fans in the ensuing years, but even still, none of them appreciated his cleverness. 

He remembers scoffing that first day back when Liam suggested that Derek had watched Stiles’ videos. Now he wonders if maybe it wasn’t so far-fetched an idea after all. Derek obviously knows about his porn “career”; is it possible he’s actually watched one or two of them?

_ S: Clever name, isn’t it? _

_ D: I should have known you were gay when you couldn’t stop talking about Jensen Ackles’ ass. _

_ S: I’m bi, thankyouverymuch. And aww, Der-bear. You jealous? You know Jensen’s ass doesn’t hold a candle to yours. _

_ D: I’m assuming I should be flattered. _

_ S: Nah. Compliments are a dime a dozen to you, I know you don’t even pay attention to them anymore. _

_ D: I pay attention when they come from someone who matters. _

_ S: Um, Derek, I hate to be the one to tell you this, but that was what’s known as flirting. You should be careful, wouldn’t want to start giving people the wrong idea. _

_ D: No, I wouldn’t.  _

_ S: Okay… Okay, so, you know my porn name, which means you clearly know how I paid my way through college.  _

_ D: I may have stumbled upon a video or two.  _

_ D: Or a hundred. _

Stiles’ breathing hitches and he feels a touch light-headed. Okay, this is really happening. This is not a drill, there is flirting. Derek’s watched his videos, and he’s flirting. Derek has watched him getting his ass stuffed with cock on the reg, and  _ he’s still fucking flirting. _

Play it cool, Stilinski.

_ S: Which one’s your favorite? _

_ D: Too many to choose from. _

_ S: You’re blowing my mind right now, you realize this, right? _

_ S: I thought you were straight. _

_ D: You should know better than to assume, Stiles. _

_ S: Point taken. So, what did you think? _

_ D: I kept watching, didn’t I? _

_ S: Apparently. Want to watch one together? _

And okay, that’s out of his fingers before his brain can process the offer. Stiles doesn’t watch his own videos. It’s weird, and not at all a turn on. But yet, here he is.

_ D: I could be convinced. _

_ S: Will you give me a play-by-play? _

_ D: Weren’t you there? _

_ S: Funny, fucker. I want to hear what you think as you’re watching it. _

_ D: You know how I feel about talking.  _

_ S: You couldn’t pony up some words for a special occasion? _

_ D: Let me know when it’s a special occasion, and I’ll see. _

_ S: You’re such a dick. _

_ D: Like we didn’t both already know that. _

_ S: So, tomorrow? _

_ D: Tomorrow. _

When Stiles tosses his phone on his dresser, he’s got a grin splitting his face from ear to ear. This isn’t at all what he’d expected when he ignored the butterflies in his stomach and sent that first text, but he couldn’t be happier about how it’s turning out. 

\-----

Stiles refuses to admit that he's anxious and jittery all day long, though Liam is quick to point it out. Mason is trying to be nice when he asks if Stiles is okay, but it's actually kind of the thing that pushes him over the edge into freak-out territory. He blames it on the fact that he stopped taking his meds his last couple years of college, and his impending employment has him more rattled than he's been in awhile. 

It doesn't fool Scott or Liam, of course, and they both give him skeptical looks as Mason bobs his head in understanding. Stiles can't handle it anymore, so he begs off the remainder of their pack bonding day and flees back to his apartment. 

It's ten on the nose when his phone rings, and his hand is shaking so hard he's doubtful he'll be able to pick it up without dropping it. Which is ridiculous, honestly; he spent years having sex on camera, nerves should be a long-distant memory. But of course this is different, because it's _Derek_. He's about to watch porn with Derek _Hale_. He's about to watch porn in which he is an _active_ _participant_ , with the man who he thought of during the filming of every single one of those videos. It doesn't matter which one they watch, he imagined Derek in the place of his partner. 

He's so lost in thought that it takes him a moment to realize his phone has stopped ringing, and he dives for it in a panic, snatching it up and hitting redial. It rings three times, and he's holding his breath, wondering if he fucked this up before it even began. 

“I thought you'd changed your mind,” are the low, soft words that greet him, the voice uncertain, and Stiles eases back on his bed, equanimity restored. Derek’s anxious, too. They're on a level playing field, and Stiles isn't some insecure, inexperienced kid anymore. 

“Nope, just too wrapped up in my own head,” he admits, and the honesty doesn't feel awkward. It feels settling, and he knows it's not just for him when Derek lets out a slow exhalation of breath. 

Stiles had wondered if it would be weirder to watch together over the phone, rather than in person, but he figured there would be less pressure this way. He didn't know what Derek's sexual experience was like, with men at least, and he didn't want him to feel like he had to jump Stiles because they were watching porn and turned on. 

He  _ hopes  _ Derek will be turned on, anyway. 

Derek takes a slow, deep breath before asking, “Do you have a favorite?”

_ Yes,  _ Stiles’ brain answers immediately, but his mouth remains surprisingly still. It wasn't until college that Stiles became confident in his ability to be a commanding top, so high school was spent imagining Derek bending him over and fucking his ass hard. The first time he topped Ryan, however, he finally allowed himself to fantasize about being the one to dominate Derek. He imagined the werewolf laid out underneath him, his cock a deep red as Stiles fucked into him, until the pleasure became so overwhelming that his release spurted over both of them. 

That particular video, while not his best, had the distinction of being his unequivocal favorite. 

“There's this one with me and two other guys,” he answers instead, not quite ready for Derek to know how much he wants to fuck him. “I'm in the middle.”

“There were a couple of those,” Derek reminds him, and fuck, he wasn't teasing when he said he'd watched a lot of Stiles’ videos. “Are you talking about the one with the two brunettes, the one with the brunette and the blonde, or the one with the blonde and the redhead?”

“Jesus, how many times have you watched these?” he blurts out. 

“A few,” he confesses, voice barely a murmur, and Stiles goes lightheaded again. His cock is already hard, pressing insistently against the zipper of his jeans, and Stiles slides the zipper down. Derek inhales sharply. “Are you taking your pants off?”

Stiles grins, even though Derek can't see him. “I need the room already.”

“I've seen you naked. You need the room all the time,” Derek remarks off-handedly, and Stiles is speechless. He isn't unaware of his size, but for Derek to comment on it is unexpected. 

Since he doesn't know what to say, he ignores it. “To answer your question, the one with the brunette and the blonde. Ryan and Kirk,” Stiles adds, even though he doubts Derek wants introductions. “Ryan was my first partner.”

“I know,” Derek replies, as if there’s nothing Stiles can tell him that he wouldn't already know, and fuck, his cock likes what his brain is hearing. “All of your earlier videos were with him.”

_ Don't come, don't come,  _ he chants to himself. “Have you made a career of studying mine?” he asks instead, allowing the sly, flirty tone to take over. 

“I had a lot of time on my hands,” Derek answers, and Stiles can almost hear his shrug. “Among other things.”

Stiles knows exactly what he's talking about, and the idea of Derek stroking himself to orgasm while watching Stiles have sex… It's almost too much for him. “I found the link to that particular video,” he says instead. “I'll text it to you.”

“I already have it queued up,” Derek informs him, tone amused, and Jesus, Stiles wants to fuck the smirk that he  _ knows  _ Derek is wearing right off his smug face. 

Stiles tries not to feel uncomfortable as he hits play on the video. It starts out with him and Kirk making out on the bed, Kirk’s hand on his dick, moving with firm strokes. Stiles tips his head back, moaning in soft little pants, and Kirk kisses down his throat before rolling them over and straddling Stiles’ thighs, moving down until his mouth closes over the head of Stiles’ cock.

“This is really fucking weird,” he confesses a half a beat later, and Derek is quiet for a moment.

“We can turn it off.”

“Fuck that. I want to hear what you have you to say.”

“I could tell you what I think of any video you’ve ever made without having to watch it again,” Derek counters, voice rough, and that seals the deal.

“Yeah, but I want to hear you while you’re getting off to it,” he says, confidence spurring him to bold words, and he doesn’t even feel anxious through the few seconds of silence. When he does hear something, it’s the harsh, shuddery sound of an inhale against the background of a zipper rasping quickly down. “Is your dick out?”

Derek groans softly into the phone, in time with Stiles’ groans on screen, and he thunks his head back against the wall in disbelief that this is actually happening. “Everything’s out,” Derek replies huskily, and Stiles bites his lip against the mental image. “I’m fully naked.” A muffled pop sounds in the background, and then Derek hisses into the phone. “And I’ve got my hand on my dick.”

“Jesus,” Stiles breathes, reaching for his own and stroking it roughly. On screen, he’s fingering Kirk’s ass open, fingers dripping lube while Kirk bucks back onto his long fingers, and he can hear Derek groaning appreciatively. “Talk to me, Der.”

“Your fingers are obscene,” he mumbles. “Every time I watch you finger someone open, I can’t help imagining what it feels like.”

Stiles scrambles to squirm his way out of his jeans while trapping his phone between his ear and shoulder, because just having the zipper down isn’t enough room for him anymore. When he’s flat on his back with his hand wrapped around his cock, he exhales on a soft whimper. “The only thing better than having fingers in my ass is having a cock in it.”

“You like taking a dick in your ass, don’t you?” Derek groans, and Stiles’ hips arch reflexively.

“I love both,” he clarifies, fist stripping his cock several times in a row before drifting down to his balls and squeezing gently. “I love riding a gorgeous dick, but I love fucking a gorgeous ass, too.”

“Stiles,” Derek breathes, and Stiles’ cock jumps. “Jesus, do you have any idea what you do to me?”

“No, but I know what I’d  _ like _ to do to you,” he teases playfully. “What do I do to you?”

The video has been all but forgotten, and when Stiles glances at it he sees it’s progressed to the point where Ryan joins them, but is only watching Stiles fuck Kirk while he fists his own cock. Stiles recalls how awkward it was to film the part where Ryan mounted him while he was fucking Kirk. Threesome scenes were hard to film, but got a lot of enthusiastic response on the site, which was one of the reasons Stiles had suggested it for tonight’s adventure. Unsurprisingly, it’s only served as a catalyst for Derek and Stiles, and he wonders if Derek is even watching it anymore.

“Der?” he prompts, when it seems as if Derek has forgotten the question.

“You make me want things I never knew I could want,” he confesses.

Stiles’ brain is spinning, but in a good way. “Like what?”

“I’ve always…” Derek hesitates, and Stiles pounces on it.

“What?”

“I’ve always wondered what it feels like. To do the things you’ve done.”

“Derek…” Stiles trails off, not knowing how delicate of a question this is, but knowing he doesn’t want to fuck anything up. “Do you have any sexual experience with men?”

The silence stretches, which gives Stiles his answer, but he waits patiently for Derek to be comfortable saying the words aloud. “No,” he admits finally. “I’ve never really wanted to do that with another guy. Until you.”

Stiles is blown away, not only by the honesty, but by the thought that he’s the guy who had turned Derek from his literal straight and narrow. “I’m going to teach you something tonight, Der. Then I’m going to teach you a lot more when I’m able to do it in person.”

“Oh yeah?” Derek’s voice is both interested and guttural, and Stiles grips the base of his cock to keep his orgasm at bay. He wants this to last. “What are you going to teach me?”

Stiles grins, his voice going dark and deep. “I’m going to teach you how to use those thick, beautiful fingers to work your ass wide open, and then I’m going to teach you how to finger yourself until you come so hard your brain hurts.”

The wanton sound that Derek emits makes him ache with need. He wants to show Derek everything, all the ways men can please themselves and each other. And he will, he promises himself; tonight is simply the first lesson.

He turns down the sound on his laptop and pushes it to the side of the bed so he can wiggle down into a comfortable position, letting his legs splay out. His cock is already hard and he grabs for the lube bottle, pouring enough out to slick himself up, and he thumbs at the head to smear the drop of precome beading there. “What are you doing?” he asks, wanting Derek to get warmed up and comfortable before diving into the new stuff.

“I’m stroking myself,” he answers, almost on a whisper, and Stiles takes a steadying breath.

“Come on big guy, don’t get shy on me now,” he teases. “Don’t be afraid to tell me everything. I like details.”

There’s another moment of hesitation and Stiles wonders if he’s pushing Derek too far. Then, Derek lets out a long, slow breath, and Stiles is gripping himself just a little bit tighter. “My dick is so hard right now,” he admits, and Stiles bites his lip. “Every time I stroke up, I play with the slit and imagine it’s your tongue.”

Holy God, this man is going to kill him. “Next time,” he promises, voice throaty and aching. “I want to taste every damn inch of you. And not just your dick,” he adds, mouth going dry at the thought of spreading Derek’s cheeks and tonguing his hole. He doesn’t know if Derek will be amenable to it, but it’s the first thing on his list of fantasies.

Derek groans, his breath catching, and Stiles fucks up into his own fist at the sound. “I want you to taste me,” he rasps, “and I want to taste you. I want to feel the weight of you on my tongue.”

“Fuck,” Stiles hisses, letting go of his erection in order to not spur his orgasm on. He still has to talk Derek through his first lesson in the Stiles Stilinski Sexual Education training course, and this isn’t about his pleasure right now, anyway. It’s entirely about Derek. “Are you relaxed right now?”

“The exact opposite. My stomach muscles are tight because I’m so close to coming.”

“Stop touching yourself, then,” he instructs, and Derek lets out a whine, and fuck, that should not be as hot as it is. “I want you to relax for a minute. Take deep breaths, sink back into the mattress, and focus on not tensing up.”

“You’re evil,” Derek pouts, and Stiles feels kind of like the Grinch did when his heart swelled three sizes. There’s some quiet breathing on the other end of the phone, and Stiles feels himself matching his breathing to Derek’s. His erection is ignored for the time being as the two fall into sync. “Okay, I’m relaxed now.”

_ Show time. _ “Do you have your lube?” He hears a soft pop on the other end of the phone, the same as earlier, and he realizes Derek was lubing his cock up before. Stiles can imagine Derek slowly stroking himself, and he fights back the little noises that want to escape his throat. The click of the cap shutting snaps him out of his reverie, and his voice is rough when he speaks. “Okay, warm the lube up between your fingers a little bit.”

“I know how to use lube, Stiles,” Derek snorts, and Stiles grins as he imagines Derek rolling his eyes. It’s nice to know that sex won’t completely change them. “Okay, it’s… Well, it’s not warm, but room temperature at least.”

“Okay, I want you to reach down and press one of your fingers to your hole,” Stiles commands, although his voice is a little shaky as he does. “Work your fingertip in a circle, massaging the ring of muscles. You’ll tense up at first, which is why I wanted you relaxed to start, but it will start to feel good and you’ll find yourself opening up.”

“I feel stupid,” Derek mutters. “I’m all hunched up and sticking a finger in my ass.”

“Not if you’re following directions, you aren’t,” Stiles contradicts breezily. “Because I said to massage the muscles, not jam your finger in your asshole.”

Derek snorts again on the other end of the line, but he falls quiet. Stiles can only imagine that he’s following directions, for once in their long history. A small groan bubbles up over the phone and Stiles can feel electricity thrumming through his skin. “What now?” he murmurs.

“Now I want you to  _ gently _ press your finger inside,” Stiles coaches, and his breath stutters in his chest when Derek’s does. “Go as far as you comfortably can, but no farther. There are no medals for hurting yourself. This is supposed to feel good.” He waits, and is rewarded with the sound of Derek breathing heavily. “When you’ve gotten used to the way it feels, circle it around. Pull at the rim of your hole so it starts to stretch. Push in a little deeper if you want, pull out, push back in. They call it finger-fucking for a reason.”

“Jesus,” he breathes, and Stiles can’t stand it anymore; he reaches down for his own cock, which is now weeping steadily, and he rubs through the precome dripping from the tip. “Is this it?”

“Not even close,” Stiles promises darkly. “How are you feeling?”

“Good,” he admits, “but not good enough.”

“Add a second finger,” Stiles instructs, and the bitten-off gasp when Derek complies is enough to make Stiles’ dick jump in his hand. “Keep doing the same thing. Work yourself open, stretch your hole, make sure you’re lubed up enough that it’s a slick slide. You shouldn’t be feeling any kind of friction or resistance from skin sticking to skin.”

“That’s not a problem,” he assures Stiles. “I’ve got lube dripping from me.”

“Jesus  _ fuck _ , Der,” he swears. “You’re going to make me come all over myself.”

“Promise?” he counters breathlessly, and Stiles is half-tempted to throw on a pair of sweats, jump in the Jeep, and race to Derek’s house. The more rational part of his brain tells him that what they’re currently doing is still sexy as fuck. Derek is learning himself without Stiles’ physical interference, and that’s a good thing. There’s plenty of time for the rest of it.

“How are you feeling with two fingers?” Stiles asks, edging his own fingers down until they’re cupping his balls, rolling them around in his palm. 

Derek huffs out a laugh. “I’m a werewolf, Stiles. I don’t need all the babying you’re talking me through. I was fine with two, and moved on to three.”

“How does it feel?” he murmurs, and Derek inhales sharply.

“Fucking fantastic,” he confirms on a rush of breath as he exhales. “I never knew I could be stretched so wide open.”

Stiles lets out an inhuman groan. “You’re killing me, Hale. I want to see.”

“I’d take a picture, but I’m pretty sure even someone as flexible as me couldn’t twist to get the proper angle,” he laughs, though it’s choked off by a moan a split-second later. “I could take a picture of something easier to reach?” he offers, tone questioning, and Stiles is tempted. He’s  _ so fucking tempted. _ But...

“I want to wait until I can see it in person,” he decides, albeit reluctantly. “I don’t want to be teased by a picture I can’t touch, or taste.”

“Fuck, Stiles, I’m so close,” Derek bites out, and Stiles snaps to attention. He fists his own cock tightly as he thrusts up into it, relishing the glide of palm against velvet and iron. Then there’s a thump and a muffled curse before Derek sounds not quite so close and intimate. “I can’t fist myself, have my fingers in my ass,  _ and _ hold a phone,” he informs Stiles, who snickers, “so you’re on speaker phone now.” Stiles can hear him flop back against his pillow and the groans begin tumbling over each other, and holy shit, Stiles is going to come any second.

“Fine by me,” he pants, finally chasing his orgasm instead of trying to hold it off. “Tell me what you’re doing.”

Noises and curses and pleas are tumbling over Derek’s lips and then Stiles hears a sound that might be squelching, and his lower back tenses as his balls tighten up. “Fuck, Stiles, Jesus, I have three fingers in my ass and I’m all but riding them. It’s incredible, I had no idea it could feel like this. My dick is so hard I could pound nails with it.”

“God, Derek, I’m going to come,” Stiles whimpers, and he’s stripping his cock as quickly as he can, feeling the tremors starting and the ache of the chase in his throat. “Are you close?”

“Shit, Stiles, you have no idea,” Derek moans, and his voice gets farther away. Stiles is picturing him planting his feet against the bed, arching up and over as he frantically fucks down onto his fingers. “I’m almost there!”

“Come for me,” he begs, needing to hear Derek’s release before his own overtakes him. “I want to hear you come while you’re fucking those thick fingers,” and that, apparently, is what does it for Derek, because he groans, long and low and rumbling, and Stiles follows him right over the edge.

Come spills all over his hand, jetting onto his chest and painting it in stripes and splatters and puddles, and he’s shuddering as he continues to fist himself, squeezing every last drop from his twitching cock. He can hear Derek breathing harshly as he comes down from his own orgasm high, and when Derek groans softly, he knows he’s just as sated and happy as Stiles himself.

“Jesus, Stiles.”

Stiles doesn’t respond; he’s pretty sure Derek’s statement doesn’t require one. Instead, he smiles and settles back onto his pillow. They’re only quiet for a moment when his phone chimes, and he pulls it away from his ear to check the incoming text from  **Sourwolf** . He promptly drops his phone. “Fucking hell, Derek!”

Derek lets out a huff of pleased laughter. “I take it you like it?”

True to Stiles’ request, Derek’s dick is nowhere in sight. Instead, it’s a longshot of his chest and abs, covered in more come than Stiles knew was possible. He’d been working in porn for years and had never seen anyone come so much. “This is a wolf thing, isn’t it? Normal human people can’t come that much.”

“I don’t know, it’s not like that was something I discussed with my parents,” Derek points out wryly. “But it’s normal for me.”

“If I wasn’t completely spent, I’d already be on my way over to your house for round two,” he blurts out, and Derek chuckles outright. 

“Looking forward to it,” he says fondly, and Stiles feels a little warmer. “Talk to me until one of us falls asleep?”

It’s Derek who falls asleep first, and Stiles stays on the phone for a little while, just listening to him breathe. The smile that curves his face is gentle, happy, and it makes him wonder if he’s ready to fall in love with Derek Hale for a second time.

\-----

Stiles assumes that Derek is as eager to make their hookup physical as he is, so when Derek starts brushing him off, he's confused. The flirty, blunt behavior is gone, replaced with terse answers to his texts. 

_ S: What are you up to tonight?  _

_ D: Working.  _

_ S: I thought you were independently wealthy. When did you get a job?  _

_ D: I freelance write sometimes. I have several articles due this week.  _

_ S: You can't take some time to have a little personal break?  ;)  _

_ D: Not really.  _

_ S: Oh.  _

_ S: Maybe later, then?  _

_ D: Maybe.  _

Stiles is hurt at first, then irritated, then he mentally tells Derek to fuck off. Then he decides he's being too sensitive and texts him again. 

_ S: You've been working really hard this week. How about dinner at my place?  _

_ D: I don't think that's a good idea, Stiles.  _

_ S: You certainly didn't think that Sunday night.  _

_ D: You  _ would  _ throw that back in my face.  _

_ S: Throw it back in your face? WTF, dude? I'm not trying to be a jerk. I just don't get this sudden 180. _

_ D: I got caught up in what I wanted and didn't think about the consequences. Let's just leave it at that.  _

_ S: If that's what you want…  _

_ D: I think it's best.  _

_ S: Okay.  _

_ D: Good night, Stiles.  _

_ S: Yeah. Good night.  _

He’s trying not to be miserable, but the unexpected rejection has him bewildered. There's no way he's misunderstood Derek’s interest, and it wasn't spurred on just recently. Derek made it clear that this has been a long time coming, and his sudden change of heart is baffling. 

It takes him another three days, but he finally has an epiphany. Derek had never indicated to anyone that he was gay, and he hadn't even known how to do more than the basics as far as pleasuring himself. What if he was embarrassed to have opened himself up like that to Stiles, and was afraid to take it any further? 

Before he can talk himself out of it, he’s grabbing his keys and phone and flying down the stairs to his Jeep, crossing his fingers that Derek doesn’t get pissed off and kick him out. He keeps them crossed the entire way out to the Preserve, the site of the recently-rebuilt Hale house. Scott told him Derek had only officially moved back to Beacon Hills about a month prior to Stiles, but he’d been in and out for the previous six months while they worked on rebuilding what was totally decimated, and restoring what could be restored. Stiles hasn’t been brave enough to do a drive-by, especially knowing Derek would be able to identify the sound of the Jeep a mile away. 

It doesn’t take long before he finds himself standing on Derek’s porch, knocking firmly on the front door. The authoritative pounding of his fist belies the butterflies in his stomach; Derek is either going to be grateful Stiles didn’t give up on him, or he’s going to kick his ass ten ways to Sunday for ignoring his wishes.

He’s hoping for the former.

“Stiles.” Derek’s voice is flat, but his eyes are alive as they skim his face. “Why are you here?”

Stiles ignores the question. “Can I come in?” he asks, trying to quell the nerves so his voice doesn’t shake. Derek smirks at him, able to smell it even if he can’t hear it, and steps aside. Stiles pushes past him and stands in the entryway, looking around in awe at the inside of the house. “It’s beautiful, Der. You did such an amazing job with this place.”

“Did you come by to critique my decorating skills?” Derek drawls.

Stiles twists to make a face at Derek over his shoulder. “Don’t be a dick.”

“Didn’t we already establish that’s part of my charm?” His eyes are twinkling now, and Stiles can’t help but grin.

“It is, but that’s what makes us a good match. I’m a total dick, too.” He takes a deep breath, wondering what Derek is going to think of his next words. “Which is why it shouldn’t surprise you that I'm pretending you didn't completely shut me down in our last text conversation.”

“Stiles.” His name eases from Derek's lips in the form of a deep sigh, and he hates hates  _ hates _ how unhappy Derek looks at this moment. “Why are you doing this? It's better for both of us if we don't continue down this path we're on.”

“I don't agree,” he counters bluntly. “I think this is exactly what you need, and you're too damn afraid to let yourself have it.”

Derek's eyes are dark and unreadable. “Are you going to do whatever you damn well please, regardless of what I think?”

“Of course not!” Stiles is horrified at the thought.  “If you don't want this, if you don't want  _ me, _ say the word and I'll turn around and go home.” He takes a tentative step toward Derek and, encouraged by the spark of fire that lights his eyes, another, and another, until he's standing directly in front of Derek. “Can you?”

“Can I what?” The words come out roughly, his voice hoarse as he locks his gaze with Stiles. 

Stiles doesn't look away. “Can you tell me you don't want me?”

He holds his ground as Derek struggles to answer, but Stiles knows it's a losing battle even before he lets out a slow breath and shakes his head. “No. I can't, and you know it.”

Stiles takes the final step to insinuate himself against Derek’s chest, reaching up to cradle his jaw, and leans forward to press his lips gently against Derek’s. When he pulls back, Derek is staring at him with eyes full of need. “Let me do this for you, Der, please. You’re almost thirty years old and you’re just now starting to explore the things you want. Let me be that safe space for you. I’m here to do anything and everything you’ve ever fantasized about, anything you’ve ever been curious about. I have almost no boundaries when it comes to sex, except watersports, and I want to be the person you explore those desires with.”

He’s unprepared when Derek’s arms come up to band around him fiercely, his mouth dropping to claim Stiles’ in a heated kiss. He gives himself over to it, letting Derek set the tone and the pace of the evening, but his blood is racing and he feels the thrill of surrender. Whether it’s Derek’s or his own, he doesn’t know.

When Derek finally breaks the kiss, both take a few moments to just breathe each other in before Stiles grabs Derek’s wrist and tugs him toward the stairs. “Eager?” Derek teases him, and Stiles flashes a wink but doesn’t answer as he guides him toward the bathroom. It’s instinct; he’d explored the burned-out shell of Derek’s family home when he was a teenager, and he was familiar with where the rooms were. He guesses that Derek wouldn’t have changed much, and at least as far as the bathroom goes, he’s not wrong.

The look of surprise on Derek’s face when Stiles pulls him into the bathroom is worth it. “Strip,” he commands softly, as he starts to do the same. Derek hesitates, but as Stiles tugs off his shirt and throws it to the floor, he suddenly moves. They’re both pulling off their jeans, followed by socks and underwear, and soon they’re completely naked. Derek’s eyes are dark with arousal as his gaze travels the length of Stiles’ body, and Stiles stands still, allowing him the freedom to visually assess everything he wants. 

He waits until Derek’s eyes finally land back on his, a faint flush lighting his cheeks and, adorably, the tips of his ears. “We’re going to get you clean,” Stiles explains, “get you relaxed, and ready. You’ll feel more comfortable when we head for your room.” The pink deepens, but Derek simply nods as Stiles reaches into the glass-walled stand-up shower and turns the taps on. It takes a few moments to adjust, but when Stiles is satisfied with the temperature, he gestures for Derek to precede him into the shower.

The heat of the water hitting him makes him moan a little, and Derek swallows as he watches the expressions flitting across Stiles’ face. The shower is roomy, but Stiles pretends it’s just big enough for the two of them and presses his chest to Derek’s as he reaches behind him for the bottle of shampoo. “I’m going to wash your hair,” he informs Derek, who has yet to say a word. That’s okay, Stiles thinks. He wants to pamper this man who so desperately needs and deserves to be pampered. 

Pouring a capful of shampoo into his hand, Stiles eases back into Derek’s space to replace the shampoo bottle. He works the shampoo between his hands, sudsing it up a little, and then slides his fingers into Derek’s hair. The wolf groans a little, closing his eyes and tipping his head back as Stiles works his hands through the thick raven-colored strands, massaging his scalp and working the shampoo into his entire head of hair.

Derek’s throat works convulsively when Stiles’ blunt nails scratch against his scalp, migrating from the top of his head to the crown, down the back of his head until he’s playing with the short hairs ending where the base of his skull meets the nape of his neck. He whimpers a little when Stiles tugs at those hairs, and his eyes pop open. “I want you to look at me,” Stiles whispers over the pounding rush of the water, and Derek watches him as if his gaze is pulled to him like a magnet. “Tell me how this feels.”

“Fucking amazing,” he groans. Stiles nudges his hips against Derek’s and finds the evidence that he does, in fact, feel fucking amazing at the moment. “I want more.”

“You got it,” Stiles promises, and he reaches for the bar of soap and the washcloth hanging over the bar inside the shower. He lathers up the cloth, then slowly slides it over Derek’s chest, trailing it over the lines of his muscles and each of the ridges and valleys in the planes of his skin. When he finally reaches his navel, he draws the cloth back up, grinning at Derek’s noises of protest. He takes the same infinite care of his arms and shoulders, then gestures to him to turn around. 

Stiles inhales sharply and his pulse quickens at the sight of the muscular back presented to him, and he all but worships it with his lips, drifting across the tight skin before dragging the cloth behind. He works his way down, ignoring Derek’s soft gasps and the way his muscles are tensing and bunching under his tender ministrations. When he gets to Derek’s ass, he pauses, just staring at it in awe. When he sinks to his knees, Derek starts to turn around, but Stiles waves him back into position and he reluctantly turns away. 

Stiles can’t help himself; he leans forward and sinks his teeth right into the top of Derek’s cheek, feeling the flex of the muscle and skin under them and biting gently. Derek fucking  _ growls _ and Stiles is light-headed with desire, but he doesn’t hurry his pace. He resumes washing, taking care to thoroughly clean Derek’s hole even though he tries to pull away in what Stiles presumes is discomfort or embarrassment. The cloth is quickly discarded and Stiles grabs the second one, lathering it up and continuing his journey down the backs of Derek’s thighs to his calves, massaging his fingertips into the tendons until he reaches the man’s feet.

“Turn around and grab my shoulders,” he tells Derek, and he does without hesitation. Stiles feels heady as he lifts one of Derek’s feet in his hands, feeling the man brace down against him to keep his balance, and uses the cloth to get between each individual toe. When he lowers the first foot, Derek lifts the other automatically, and Stiles takes the same care with it as he did the other. Stiles inhales unsteadily, working his way back up Derek’s shins and thighs until he’s face-to-cock with Derek’s erection. 

Ignoring it for the moment, as well as Derek’s barely-audible pleas, Stiles slides the cloth along the creases between the tops of Derek’s thighs and his groin, paying attention to every detail. He cups the cloth over Derek’s balls, rubbing gently and cleaning around the entire area. Finally, he wraps the cloth over Derek’s cock, stroking him loosely with the intent of cleaning-and maybe a little teasing. It’s a desperate thing, this need to bend his head and swallow that pulsing length, but not here. 

Rising, he guides Derek fully under the spray, pressing his chest to Derek’s back and dropping his head so that his cheek is nestled against Derek’s shoulder while he rinses the soap out of his hair and off his skin. Stiles gets a little soap in his eyes as it runs from Derek’s hair down his neck, but he can’t bring himself to care. “Stiles?” he asks quietly, and Stiles mumbles an assent against his shoulder. “Have you ever done this before? The showering thing? And the, uh, the washing thing?”

“Nope,” Stiles replies, lips moving against Derek’s shoulder. “This is a first for me.” He can feel Derek relax under his touch, and Stiles wonders if it was important to him that he not be the only one experiencing new things. Stiles could tell him that it’s new to him to be in love with the person he’s sleeping with, but it’s not something he’s ready to share.

When Derek is completely clean, Stiles takes the briefest of moments to scrub himself. Derek protests, wanting to return the favor, but tonight isn’t about Stiles. He wants to move this along to the bedroom so they can start fulfilling all of Derek’s fantasies.

As they step out of the shower, Stiles snags a couple towels. “Dry off thoroughly,” he tells Derek, quirking a smirk at him. “Despite what porn may tell you, trying to have sex when you’re still damp isn’t the most comfortable thing in the world. There’s a lot of skin sticking to skin, and not in a sexy way.” 

They dry themselves off and when Stiles turns to hang the towels up, Derek eases in behind him, dropping his face to Stiles’ shoulder. Stiles can feel the blunt edge of Derek’s teeth against his skin, and he throbs when he whispers, “Do it.” 

“Are you sure?” Derek asks in surprise, and Stiles nods, swallowing hard.

“As long as it won’t result in a brand-new, very wolfy Stiles by tomorrow, biting is perfectly acceptable,” he reassures him, and almost before the words are out of his mouth, Derek’s teeth are sinking into his skin. He jerks against the slight pain and groans as it fades into something achy and delicious. Derek’s lips are on his throat, soothing over the reddened skin even as his beard continues to abrade it, and Stiles has to break away from him, panting. “Jesus fuck, Der, that’s hot, but I really don’t want to come before we’ve even made it out of the bathroom.”

“Spoilsport,” he pouts, and Stiles snorts out a little huff of laughter. Pouting Derek is fucking  _ adorable _ .

He waits until they’re in Derek’s room before he breaks the silence. “This is your night, Der. What do you want me to do?”

It’s a powerful thing to see Derek Hale nervous and unsure in front of him, and he vows to do everything in his power to make Derek feel comfortable, to feel loved and cherished and beautiful, no matter what he wants. Hesitantly, he answers. “I want everything, Stiles. I want everything you can possibly think of.”

“Fuck, Derek,” Stiles groans, his head tipping back as his throat works convulsively. “There are so many things I want to do to you.”

“Do them all,” Derek breathes, dropping his face into the curve of Stiles’ throat and inhaling his clean scent. “If tonight is truly about me, give me everything.”

“Lie back,” Stiles commands, eyes blazing, “and get comfortable.” Derek follows orders immediately, spread out on his back and looking up at Stiles with trust in his eyes, and Stiles almost can’t. He’s not good enough for the incredible man opened up before him, and he has a moment of panic that he’s going to ruin this.

“Stiles.” Derek’s voice is low, soothing. “I want this, with you. Isn’t that what you asked me earlier? I don’t just want this, I don’t just want you. I want  _ this _ with _ you _ . Don’t freak out on me now.”

The softly teasing words bring Stiles back to the present, and the open, vulnerable expression on Derek’s face has him falling forward, slotting their bodies together as their mouths meet. It’s all hunger and teeth and ferocity, and it’s not a particularly suave or skilled kiss, but it’s heat and desire and it both soothes and fuels the growing ache in his throat. “I’m going to give you everything, Der. I promise. Everything I have in me to give.”

He doesn’t wait to see Derek’s reaction to the “this isn’t exactly a fuckbuddies moment for me” confession; instead, he shimmies down Derek’s torso and thighs until he’s hovering over his cock, which has softened slightly in the time between the shower and now. It makes it easier to slide his mouth down a significant portion of it, working the length with his tongue and lips, and Derek groans heatedly, his fingers clenching into the bedsheets. 

Stiles had assumed that Derek knew what it was like to get a blow job, at least, even if it had never been from a guy, but now he wonders-has he ever? Kate wasn’t the type to worry about anyone else’s pleasure, and Jennifer manipulated him with sex and magic. A hummer wouldn’t have been necessary to seal the deal. Possibly with Braeden, but he somehow doubted their relationship was ever about anything more than using each other’s bodies to get off as quickly as possible.

“Tell me what you like, big guy,” he coaxes after he pulls off, using his fist to lazily stroke up and down the hardening length. “I want to know what you like, what feels good and what doesn’t.”

“I can’t imagine anything you do  _ not _ feeling incredible,” Derek informs him, a soft, fond smile curving his lips, and Stiles is struck in that moment that this is true intimacy, beyond anything he’s ever experienced. “But to answer your question, I love the way your mouth feels on me. That wet heat makes my toes curl.”

Stiles doesn’t hesitate before dropping his head back down, taking Derek’s now fully-hard cock back between his lips, and his chest tightens imperceptibly when Derek drops a hand onto his head, running his fingers lazily through his too-long hair. He arches into the touch, relishing the feel of Derek’s fingertips massaging against his scalp, and hums happily. Derek arches unexpectedly against the new sensation, and Stiles takes the sudden thrust into his throat without missing a beat. 

As he swallows more of Derek’s length, he circles his thumb and forefinger into a ring around the base of Derek’s dick, tightening as he pulls upward, and Derek chokes out a gasp when Stiles’ throat constricts around him. Stiles’ eyes are watering slightly, but this is nothing he’s not used to, and he continues to bob his head in tandem with the upstroke of his fingers. Derek’s groans grow in frequency and volume, and Stiles impishly pulls away, letting Derek’s cock escape his mouth and then flop back to smack wetly against his cheek.

“You’re evil,” Derek rasps, and Stiles smiles modestly. “I was so close.”

“Do you really want to come this soon?” Stiles questions, arching one eyebrow. He might not have the Hale Eyebrows, but he’s learned to use what he has rather effectively. “There’s so much left to do.”

“Like what?” Derek asks, voice eager, and Stiles’ heart thumps at how much he wants this. At how much he loves the man spread out beneath him.

“Like this,” he answers, brushing off any thoughts of love lest he make an ill-timed declaration. He gets down on his stomach, propped up on his elbows, and gently pulls Derek’s ass cheeks apart. Derek automatically tenses, not used to someone being so intimately close to him, and Stiles stills. “You okay, Der?”

After a few moments, Derek’s thighs relax and he nods. “Yeah,” he rasps. “More than okay.”

Stiles goes slowly, letting Derek understand his intentions, and when his tongue darts out to flick against Derek’s rim, the older man doesn’t even flinch. Encouraged, Stiles moves in a little closer, tugs at Derek’s hips until he’s curled and arching up a little more, opening himself up to Stiles’ exploring tongue.

Derek chokes on a strangled groan when Stiles forgoes being tentative and dives straight into rimming him with enthusiasm. His tongue presses into the tight rim, massaging and circling, pushing deeper with every pass, and he can feel Derek relax and tense in turns. 

“Jesus, Stiles,” he grits out, flexing his hips up as if chasing the motions of his tongue. “You're trying to kill me, aren't you?”

Stiles pulls back, feeling immensely satisfied when the air hits the wetness over his mouth, chin, and cheeks. With the way Derek's eyes dilate and a low growl rumbles up out of his chest, he's pretty confident Derek is enjoying the sight as well. 

“Nah,” he replies breezily. “I want you alive and responsive so I can make you come harder than you ever have before. Multiple times,” he adds, reveling in the way Derek's eyes flutter shut and he doesn't even bother to restrain his groan. 

He snags the bottle of lube off Derek’s nightstand-which, considering Derek had no idea he was going to come over tonight, meant he had either recently jerked off or was planning on doing so soon, and damn does his cock like that thought. “Have you been practicing fingering yourself?” he asks conversationally, not wanting Derek to feel ashamed in any way. 

“A couple times,” Derek admits, eyes avariciously watching as Stiles pours lube out onto his fingers, rubbing them together to take the chill away. “I wanted yours instead, though.”

“Funny, I wanted the same thing.” He grins darkly, and before Derek can react, he's pressing the tip of his finger to Derek's slightly-loosened hole. He arches, and Stiles’ cock jumps at how responsive Derek is. “Fuck, baby, you're so good for me,” he breathes, the endearment slipping out unconsciously. “Look at how you're opening up for me.”

“I need more,” Derek gasps, chasing Stiles’ fingertip, trying to take him in deeper. “Fuck my ass with those long, gorgeous fingers.  _ Please _ ,” he begs, and who is Stiles to try to deny him? 

He slips one finger inside, Derek’s rim clutching tightly and drawing him in. He strokes shallowly at first, getting Derek accustomed to the different feel of Stiles’ fingers versus his own, watching Derek in fascination as his eyelids flutter and his throat works convulsively. “You ready for another one, baby?” he prompts, and Derek chokes out his assent, so Stiles eases his middle finger in along with his index. 

Despite having practiced a few times, Derek is still incredibly tight. Stiles can feel his hole clench down around the two fingers invading it, but if the precome dripping down Derek's cock is any indication, he's thoroughly enjoying himself. Stiles thrusts both fingers in lightly, biting back a smile when Derek cries out, then withdraws slightly before thrusting right back in. 

He builds up a rhythm, and when he stops Derek immediately protests. “Someone is needy,” he says playfully. 

“You're a fucking tease,” Derek growls, bucking upward, and Stiles sighs, put-upon, before adding a third finger and driving back in. In addition, he drops his face and sucks Derek's dick back into his throat as he finger-fucks his ass. 

“Shit, Stiles!” Derek whines, and the sound shoots straight to his cock, which dribbles precome. “Fuck, I'm going to come, please don't stop!”

Stiles pulls off, his fist taking the place of his mouth and both hands stroke in tandem. “That's it, baby, come for me,” he coaches encouragingly. “I want to see the gorgeous mess you're going to make all over yourself.”

Derek's breathing hitches and he's panting, fucking himself down onto Stiles’ fingers and then back up into his mouth. Stiles debates continuing to suck his cock down for a moment, but he wants to get a sense of the intensity of Derek's climax, and see the amount of come in person, before he tries to swallow his release. 

Pulling off again, he settles back in between Derek's thighs and pulls his cheeks apart with his free hand. He's continuing to pump all three fingers into Derek's ass and his mouth joins them, his tongue spearing into the scant space left. His jaw is sore, but he doesn't dream of complaining because having Derek Hale writhing underneath him, purpling cock seconds away from erupting, is worth every bit of discomfort. 

Derek is reduced to bitten-off gasps and growls and his breathing is ratcheting up, and he’s clenching and tensing so hard that Stiles knows he won’t last much longer. With one sharp thrust and twist of his fingers, accompanied by a quick lick from his hole to his balls, Derek is spilling himself amidst hoarse, breathless cries of Stiles’ name mixed with supplication to every deity known to man.

Stiles pulls back, eyes greedily taking in the veritable fountain of come erupting in spurts and stripes, his cock pulsing and twitching with each little tremor. When he’s finally finished, the mess he’s made is both arousing and terrifying. “I’ve worked in porn for over three years and I have  _ never _ seen so much come,” Stiles informs him, in awe of the beauty in front of him. “You realize I’m never going to be able to swallow all of that, right? I mean, I’m game to try, but that’s one challenge I’m fully aware I’ll have to tap out of.”

Derek chuckles, propping himself up on his elbows. “I wouldn’t ask you to,” he replies, arching his neck and popping it with a long, lazy groan. “Jesus, Stiles. I thought I was literally going to come my brains out for a second there.”

Stiles is off the bed and into the bathroom, then back into the bedroom before Derek is even finished talking. “It certainly looks like you did,” he teases, taking the still-damp washcloth and thoroughly cleaning up Derek’s chest, abs, thighs, and cock. He’s gentle when wiping away the last dribbles of come from the head and shaft, knowing Derek is likely to be oversensitive. 

He moves to leave the bed, to take the cloth back to the bathroom, but Derek hooks an arm around his waist and tugs him back down beside him. “Just toss it in the laundry,” he commands, mouthing at Stiles’ throat. “You’re not leaving my side until I can’t move to stop you.”

“Bossy,” Stiles observes, shaking his head and clucking his tongue in mock disappointment. “What if I had plans for the rest of the night?”

“You do,” Derek acknowledges with a shrug. “They involve not leaving this bed.”

He sighs melodramatically. “I suppose I don’t have anything better to do.” Derek nips at the hollow of his throat, scraping his teeth over the skin and catching on his clavicle, and Stiles nearly comes. “You need to stop doing that or I’m going to make a mess in your bed.”

“Good,” Derek whispers, nuzzling against his shoulder and gently abrading the skin with his beard. “I want you to make a mess in my bed. I want you to make lots of messes in my bed.”

Stiles pulls back and waits until Derek lifts his head, staring at him quizzically. “What brought all this on?” he asks, knowing it probably isn’t the best time but needing to know what the hell is going on in Derek’s head. “You were all about flirting, then you cockblocked both of us. Now you’re being all possessive. Not that I mind, let’s be clear on that, but I don’t understand.”

Derek sighs, sinking back onto the bed and reclining against his pillow. Stiles remains sitting up, looking down at him while he struggles to put his thoughts into words. “I was afraid,” he admits quietly. “I thought this was just about sex for you.”

“Why would you be afraid of that?” he asks lightly, trying to keep his heartbeat steady. It doesn’t work; he can tell the moment Derek’s gaze flicks to his chest that it’s betrayed him.

“Because I didn’t think I could handle having sex with you and watching you walk away afterward like it didn’t matter,” he replies, voice even but eyes anxious. “I want more than that. I don’t want you to think this is casual.”

Stiles blinks, stunned. “Derek, this is literally the second time we’ve seen each other since I’ve been home. How do you know this is what you want?”

Derek sits up, peering into his confused gaze. “Stiles. How do you not know this has been years in the making?”

His heart is racing. He’s known for years that Derek was the one man no one in his life could ever measure up to, the one he would always look back on and pinpoint as the reason he couldn’t fall in love with anyone else in quite the same way. It never occurred to him that Derek felt in any way the same. “You’ve wanted this? I mean, before we both came back to Beacon Hills?”

“Stiles, I’ve wanted this since your junior year of high school,” Derek sighs, and holy fucking shit. “Life just got in our way before you were old enough for me to do anything about it.”

He’s speechless, for once in his life. Stiles stares at Derek, who starts to flinch and pull away, mumbling apologies under his breath, and that’s what snaps him out of it. He lunges, grabbing onto Derek’s hand and tugging it into his lap. “Jesus Christ, Derek, I never knew. How in the world could I ever expect that someone like you would be interested in the dorky spaz I was in high school?”

“Stiles, you were never just a dorky spaz,” he contradicts, eyes softening and roaming Stiles’ face lovingly. “Maybe when we first met you were like that, but you were always something more. Our lives, the supernatural, it gave you a purpose. It gave you focus. I watched you start to become someone who I knew would be an incredible man. I just wasn’t there to see it finally happen.”

“Fucking hell, Derek!” Stiles breathes, sinking back until his butt is pressed into his heels. Derek’s hand drifts over his knee, tracing little patterns that send shivers racing over Stiles’ skin. “We missed out on so much.”

“Maybe,” Derek muses. “But would you really take back everything you’ve been through to have had a couple extra years with me?”

He studies the older man, whose steady gaze tells Stiles he already knows the truth. Since Stiles isn’t one to lie to make other people feel better, he knows it’s okay to be honest. “No.” And he wouldn’t. He needed those years to grow up, to learn and explore and discover who he was away from Beacon Hills, away from the supernatural, away from Derek. It’s not a stretch to say he would never have felt like Derek’s equal if he’d become Derek’s Boyfriend straight out of high school. Now, he feels like he and the wolf are on an even keel. “No, I wouldn’t take it back. I’m grateful for it. But I’m even more grateful that I didn’t lose my chance with you to gain that life.”

“Come here,” Derek murmurs, and Stiles feels himself drawn into the circle of muscular arms, pulled tight against a hairy chest that he rubbed himself against like a cat. “I’ve been waiting five years for this, Stiles.”

“Let me make it worth the wait,” Stiles replies earnestly, and Derek smiles. It’s such a rare sight that Stiles’ heart catches in his chest, and he marvels at the blinding radiance. 

“You will  _ always _ be worth the wait.”

Stiles leverages himself to be able to fuse his mouth to Derek’s, their lips slotting together and their tongues seeking the other. It’s not as graceless and urgent as their earlier kiss; this is something soft and sweet and earnest, something speaks of a promise of the future, and Stiles doesn’t want it to ever end.

It does, but he can’t bring himself to be unhappy about it when Derek glances up at him, cheeks and ears tinting a faint pink. “I want to ride you.”

“God,  _ yes _ ,” Stiles groans, and his neglected cock, which has softened considerably, begins to plump back up at the thought that he’s going to be buried inside Derek’s ass. “I’ve thought about that for  _ years _ , Der.”

“Me too,” he admits shyly. “What do you need me to do?”

“Just sit there looking gorgeous,” Stiles tells him with a lopsided grin. “I need to prep.” He leans over to grab the lube, pouring a generous amount into the cup of his palm and then slicking his cock up with firm strokes. The pressure brings him to full hardness and he’s weeping precome again within moments. “We don’t need condoms for the traditional purpose of preventing the spread of disease,” he acknowledges, waving a hand at Derek, presumably to indicate  _ werewolf _ . “But do you want one to keep things relatively clean?”

“I told you,” Derek all but purrs, straddling Stiles’ hips and leaning in close. “I want you to make a mess in my bed.”

“Fuck, Der,” he groans. “I’m going to come before I’m even inside you if you don’t stop talking like that.”

Derek eases back, the head of Stiles’ dick bumping against his ass cheeks, and smiles wickedly. “Better keep my mouth shut, then.”

“Not too much,” Stiles protests, eyes twinkling. “I want to hear you make all those pretty noises while you’re riding me, fucking that beautiful ass down on my cock.”

“Fuck, Stiles, your dirty talk alone is going to make me come again,” he groans, and it gives Stiles pause. The dirty talk was one of the things he hated most about his previous job, but he’s surprised to realize he enjoys it, given the right setting. And clearly the right partner. “I need you to fuck me now.”

His heart is pounding as Derek eases up onto his knees, positioning himself right over Stiles’ dick. Derek plucks up the bottle of lube and deposits plenty on his fingers, then reaches behind himself to start working the lube into his ass. “Be careful, Der. I know you’re a werewolf and you heal, but I need you to take this slow. You have the control here, okay? You can fuck down onto me as hard or fast as you want, but it needs to be gentle until you’re used to the feel of being stretched.”

“You stretched me plenty with your fingers and tongue,” Derek reminds him, the green of his eyes deepening to a gleaming jade color. “I need you buried inside me.” WIth that proclamation, Derek sinks down, gasping as Stiles’ cock breaches his body. There’s resistance, instinctively, protesting the foreign intrusion.

Stiles is overwhelmed by the feel of being even partially inside Derek. “Go easy, Der,” he reminds him. “Take your time.” 

Derek mock-glares at him. “I can handle it, Stiles.” As if to prove his point, he lifts slightly, shifting into a more comfortable position, and pushes all the way down. He takes every inch of Stiles’ cock, and Stiles knows what pure bliss feels like when he’s bottoming out inside Derek Hale.

There’s a moment when both have to pause, have to fight off the orgasm that’s snaking through them, just from the sensation of being so thoroughly entwined with the other. The tight heat surrounding Stiles is like nothing he’s ever experienced; the emotions coursing through him making him feel every clench, every brush of skin against skin in a way he never knew possible. It’s enough to make him wonder if they’re so thoroughly fused together that his lungs expand with air every time Derek takes a breath.

The poetry of his thoughts is almost enough to scare him. He’s felt affection for his past sexual partners but he’s never fallen so deeply, and though he’s long since become accustomed to the constant haunting presence of Derek Hale in his heart, he couldn’t begin to understand what it’s like to be with someone you love in such an elemental way.

He has to stop himself from letting those three little words slip; though he means them, and he’s not afraid to say them, he doesn’t want to say them for the first time during sex. Instead, he smiles up at Derek. “How do you feel?”

“Do you even have to ask?” Derek breathes out. “I’m so full and it’s fucking amazing.” 

“Then ride me,” Stiles demands, and Derek does. It’s slow at first, just as Stiles told him, and he rises slowly before sinking back down. Stiles relishes every stroke, feels his breath stutter every time Derek slides back down onto him and swallows him whole. “Fuck, baby, you’re perfect,” he praises Derek, who ducks his head against a pleased smile. “You’re so good for me, you know that, right?”

Derek tips his head back and doesn’t answer, just continues to ride Stiles, moving faster and thrusting down harder. When Stiles thinks Derek’s fucking him hard enough, he starts moving his own hips and driving up to meet Derek’s downward thrusts. Moans tumble over their lips, breathing harsh and erratic as the sparks begin to unfurl and climb up their spines. 

“Stiles, fuck, you feel so fucking good,” Derek pants, working his hips faster to take as much of Stiles inside him as he can. Stiles arches his hips, fucking into him deeper, and he knows the exact moment when he hits Derek’s prostate. His mouth falls slack, his eyes pop open wide and he stares down at Stiles in amazement. 

“That’s nothing,” Stiles manages to get out, trying to grin but knowing his face is probably twisting into an unattractive grimace. He’s seen his O face, and he knows it’s not particularly sexy, but right now it couldn’t possibly matter less. His eyes meet Derek’s, and he lets a wicked expression wash over his face. “See how this feels.”

He punches up again and again, hitting into Derek’s prostate with every stroke, and Derek curls over him, panting and squeezing his eyes shut. “Fuck, Stiles, I’m going to come again,” he grates out, voice rough and wrecked, and Stiles knows exactly how he feels. One of his hands falls from Derek’s hips, where they’d been gripping so tightly that Derek would have bruises for a week if it wasn’t for werewolf healing, and circles his cock to start jacking it with smooth strokes. Derek whimpers, and Stiles is close, so fucking close, but he wants Derek to come first.

“Come on, baby, I want you to come all over me,” he pants, the sound of their hips colliding as loud as thunder in the otherwise-quiet room. “I want you to cover my stomach and my chest with all that come. Paint me with it, make me smell like you. Mark me up, so every other wolf knows I’m yours.”

And  _ that _ was apparently the sexiest thing a wolf could hear, or at least that Derek could hear. He nearly howled as his orgasm hit; his cock began pumping out wave after wave of come as he shuddered over Stiles, his hole contracting rapidly around Stiles’ dick. The pressure of the squeezing muscle clamping down on him was enough to push Stiles into his own orgasm, and his back bowed as he filled Derek with his release. 

Stiles pants raggedly through every spurt of his cock, the aftershocks racing through him almost as strongly as the initial high of coming. He throws an arm weakly over his eyes as Derek collapsed against him, wincing at the squish of the mess between their chests.

“Um, Der, as sexy as all this come was a few seconds ago, now it’s just kind of gross,” he points out, and Derek lifts up sheepishly, then eases off of Stiles. “Turn around,” he commands suddenly, and when Derek does, Stiles exhales harshly. His come is trickling down the backs of Derek’s thighs, and yeah, okay, the come is definitely sexy again.

“I think we need another shower,” Derek acknowledges dryly, and Stiles nods in agreement, making a face at the way it’s sticking in his chest hair and drying against his skin. Following Derek into the bathroom, he’s struck with the realization that this is is just one of many times he’ll be doing this. This is just another first for them.

“You’re my last first,” he says out loud, and Derek turns to look at him in confusion. “I mean, I’m going to have a lot more firsts,” he clarifies. “But you’re the last person I’m going to have them with. I won’t have another first kiss, but I’ll have the first time I wake up to see you lying next to me. I’ll have the first dance at our wedding, and the first time I hold our children, and the first time we watch one of their school plays, or graduate. Those firsts are all going to be yours.”

He doesn’t really think about the enormity of what he’s said until he sees the way Derek is staring at him, his throat working without actually swallowing, and he blushes. “Do you mean that?” he asks, voice trembling.

Stiles nods fervently. “Of course I do, Derek. I love you, haven’t you figured that out yet? I always have. I don’t want that life with anyone but you.”

He’s unprepared but not unsurprised when Derek advances suddenly, pressing him into the wall of the shower, holding him in place with his hips and chest. “You’re all my firsts, Stiles,” he murmurs, nosing into the space below Stiles’ ear. “I love you. You’re everything I could have asked for and never thought I would have.”

The emotion shining in Derek’s eyes is enough to bring him to his knees; luckily, Derek’s body is supporting him so he doesn’t fall. “It’s always going to be you and me, big guy. I promise.”

Derek smiles at him so softly that Stiles can’t breathe; he’s never felt so cherished. “And we have a lifetime of firsts ahead of us.”

**Author's Note:**

> Clotpolesonly's request was to have Stiles go away to college and get involved in amateur porn, and when he goes back home to Beacon Hills, Derek is already there. One of the wolves tells Stiles that whenever he's brought up, Derek gets embarrassed. Stiles finds out that Derek watched his videos, and asks for a play-by-play. 
> 
> Please come say hi to me on [Tumblr](https://www.tumblr.com/blog/cobrilee)! I love talking to people. :)


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